


The First And The Last Time

by smolandgrumpy



Category: Supernatural
Genre: Angst, Character Death, F/M, Fluff, Smut
Language: English
Status: Completed
Published: 2020-06-29
Updated: 2020-06-29
Packaged: 2021-03-04 03:48:22
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,239
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24977146
Author URL: https://archiveofourown.org/users/smolandgrumpy/pseuds/smolandgrumpy
Summary: The first time Dean saw her, she got out of the U-Haul and smiled at him like she really saw into his broken soul.
Relationships: Dean Winchester/OFC, Dean Winchester/Reader, Dean Winchester/You
Comments: 1
Kudos: 38





	The First And The Last Time

The first time Dean saw her, she got out of the U-Haul and smiled at him like she really saw into his broken soul.

Dean always had a thing for her. He was a goner since she moved next door.

He smiled like an idiot when she agreed to go on a date with him. And he tried to impress her, he really did. However, he hadn’t accounted for his dad to call in with another case and he had to leave her to go hunt fucking monsters. 

Y/N didn’t talk to him for a long time after that and as fucking fate has it, he had to move away. And of course he did because he had no choice and life’s never been fair to him. Not fucking once. 

The next time he met her was pure luck. They were adults now, living in a fucking bunker. Dean should have forgotten about her, but he never could, so when their route took them through her town, he couldn’t help but make a stop. They drive by her house and Sammy dropped a stupid remark. Dean couldn’t even find it in himself to care. 

He didn’t find her though. There was someone else living there. Dean knew, because he read the name on the mailbox and even walked up to the house to knock at the door just to be extra sure that she had really left. He waved his fake badge around, asked for information about the tenants that lived there before. They said the parents had died in a car crash and she had moved further into town. They also said that she worked in a diner. Dean realized that it was the diner they had their first date in.

Dean hated himself. Hated the fact that he wasn’t around to help her when the accident happened. They didn’t have cell phones back then and she didn’t have a landline either because her dad used to come around and use their phone. He wrote her a couple of letters that went unanswered, but how could she answer if they were moving all the fucking time. 

Later, he dragged Sammy into the restaurant. He felt like he was seventeen again and his heart was beating out of his chest. He knew that he would faint if he went in there on his own. Sam told him that he was acting weird because Dean never had any problems when he flirted with waitresses and fucked them in his car. Dean tried to tell Sammy that it wasn’t the same. That Sam missed the whole fucking point completely, but Sam still didn’t get it. He would never get it. Dean was not entirely sure if he got it either, to be honest.

There she was. Smiling at him, as if there wasn’t more than a decade between them. He could feel himself falling again. Dean couldn’t catch himself from falling if he tried.

He took her with him right then, didn’t even care what Sammy had to say about it. Dean was surprised that she had let him. 

Y/N had been with him ever since, and he learned more about her. Learned how she ticked, what she liked (lazy mornings), what she hated (being woken up), and he showed her too. Showed her, what he liked (her), what he hated (not her). 

He absolutely loved how she looked when she was spread out on his bed, her cheeks flushed, her hair a mess. 

Her body was a fucking wonderland and he explored new territory every day. His hands would travel up her legs and caress every inch, skin smooth like a peach with little hairs standing up from his touch. His tongue would map out new streets on the bumpy landscape, stretch marks and scars faint, but there. 

She was shy about it, but he made sure that she forgot her insecurities. Spreading more kisses around the places he knew she was not happy about. When he looked at her, he saw her tugging her lips between her teeth, eyes hungry, cheeks pink. 

Dean liked to take his time, liked to use his tongue, licking up from the depth of the valley between her thighs to the heights of the mountain of her tits and further up to the peak of her nipples. 

Y/N’d squirm below him, moaning out and arching her back, driving his face deeper into her body. 

He loved how happy she looked when he let her suck him off. It didn’t happen often, because he just loved eating her out more than loved for her to suck him. But every time she did, he was amazed at how eager she was to take the whole of him. Dean loved how she choked on his fucking cock. Loved how she looked up with tears in her eyes and her mouth full of his dick. He loved how he felt when he was inside her tight pussy. Loved how she casually leaked his cum a day or even two later. Loved the scratch mark she would leave on his back. He wore them proudly, parading them around for Sammy to see. 

Dean also loved her voice. Loved the way she begged him to fuck her harder, the way she demanded him to go fucking deeper. He loved the sounds she made when he choked her, the little whimpers and grunts. Loved how her tongue always tasted like fucking cherry to him, loved how her cunt tasted the same. He absolutely loved how she could make him come so fucking hard sometimes that he saw fucking stars. Dean loved how she can get absolutely fucking nasty in bed and be an absolute sweetheart when they were just laying on the sofa, cuddling. Dean loved all of this but—

—good things never last, do they?

No, good things never last for him. Not when Chuck still had control over his whole damn life. Chuck made him choose between either her or Sam, and she knew. She fucking knew that he wouldn’t be able to choose between them, so she walked right into the knife he was holding up at Chuck.

Dean didn’t react fast enough to pull away but he was fast enough to catch her when she fell to the floor. 

Chuck laughed before he disappeared.

The last time Dean saw her, he had tears in his eyes but she smiled and whispered that everything would be okay. Her voice was faint as blood pooled underneath her body. He couldn’t pull out the knife as it would make it worse. Sam called an ambulance, but Dean knew that they wouldn’t get here on time. 

Y/N had kept on talking, had kept reassuring him that it was okay, that she was happy. That he was the one who made her happy. 

Dean couldn’t stop telling her how sorry he was. It’s the first time he told her that he loved her. The first fucking time, and she didn’t even hear him because he was sobbing uncontrollably. He started to see that her eyes began to get empty, and felt her breathing weaken.

With one last push of her breath, she made him promise her that he would win.

Dean couldn’t tell her that a win was worth fucking nothing when she wasn’t there to celebrate it with them. He couldn’t tell her— because she had gone.


End file.
